Miconazole → 1-(p-Chlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium iodide

HRID 328633

Reaction equation

HRID 328633 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH:4]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][I:32])=[CH:29][CH:28]=1>C(Cl)Cl>[I-:32].[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N+:8]2[CH:9]=[CH:10][N:6]([CH2:5][CH:4]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:3]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:2]=3[Cl:1])[CH:7]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 4189MiconazoleHCID 3121671-Chloro-4-(iodomethyl)benzene

Product 1

HCID 867346501-(p-Chlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium iodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 Parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)-phenethyl]imidazole, 3.7 parts of p-chlorobenzyl iodide and 56 parts of methylene chloride are mixed together and stirred at reflux temperature for five hours to obtain a 1-(p-chlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium iodide product which remains in the reaction mixture. The reaction mixture is warmed to evaporate off the solvent and to recover the product as residue. The crude product is purified by washing with 2-propanol and crystallizing from a mixture of 4-methyl-2-pentanone and diisopropyl ether, to yield 1-(p-chlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium iodide; m.p. 145° -148° C.

Workup

  1. temperatureat reflux temperature for five hours

Sources & evidence

ORD record
ord-ff482ff1833744e4bc5f6dfb598ec682
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Linked notes

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